Chiral Brønsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles - Details

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Abstract：

A　new　chiral　Brønsted　acid,　generated　in　situ　from　a　chiral　phosphoric　acid　boron　(CPAB)　complex　and　water,　was　successfully　applied　to　asymmetric　indole　reduction.　This　“designer　acid　catalyst”,　which　is　more　acidic　than　TsOH　as　suggested　by　DFT　calculations,　allows　the　unprecedented　direct　asymmetric　reduction　of　C2-aryl-substituted　N-unprotected　indoles　and　features　good　to　excellent　enantioselectivities　with　broad　functional　group　tolerance.　DFT　calculations　and　mechanistic　experiments　indicates　that　this　reaction　undergoes　C3-protonation　and　hydride-transfer　processes.　Besides,　bulky　C2-alkyl-substituted　N-unprotected　indoles　are　also　suitable　for　this　system.　©　2019　Wiley-VCH　Verlag　GmbH　&　Co.　KGaA,　Weinheim

Keyword：

asymmetric catalysis; boron; Brønsted acid; heterocycles; water

Community：

[ 1 ] [Yang, K.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian, 350108, China
[ 2 ] [Lou, Y.]Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou, Zhejiang 310000, China
[ 3 ] [Wang, C.]Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou, Zhejiang 310000, China
[ 4 ] [Qi, L.-W.]Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen, 518055, China
[ 5 ] [Fang, T.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian, 350108, China
[ 6 ] [Zhang, F.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian, 350108, China
[ 7 ] [Xu, H.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian, 350108, China
[ 8 ] [Zhou, L.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian, 350108, China
[ 9 ] [Li, W.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian, 350108, China
[ 10 ] [Zhang, G.]Institute of Next Generation Matter Transformation, College of Materials Science Engineering at Huaqiao University, 668 Jimei Boulevard, Xiamen, Fujian 361021, China
[ 11 ] [Yu, P.]Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen, 518055, China
[ 12 ] [Song, Q.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian, 350108, China
[ 13 ] [Song, Q.]Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou, Zhejiang 310000, China
[ 14 ] [Song, Q.]Institute of Next Generation Matter Transformation, College of Materials Science Engineering at Huaqiao University, 668 Jimei Boulevard, Xiamen, Fujian 361021, China

Reprint 's Address：

[Yu, P.]Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and TechnologyChina

Email：

yupy@sustech.edu.cn

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Source ：

Angewandte Chemie - International Edition

ISSN： 1433-7851

Year： 2020

Issue： 8

Volume： 59

Page： 3294-3299

1 5 . 3 3 6

JCR@2020

1 6 . 1 0 0

JCR@2023

ESI HC Threshold：160

JCR Journal Grade：1

CAS Journal Grade：2

Cited Count：

WoS CC Cited Count：

SCOPUS Cited Count： 34

ESI Highly Cited Papers on the List： 0 Unfold All

WanFang Cited Count：

Chinese Cited Count：

30 Days PV： 0

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